US4335045A - Preparation of N-alkenyl-2-aminomethyl-pyrrolidines - Google Patents

Preparation of N-alkenyl-2-aminomethyl-pyrrolidines Download PDF

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Publication number
US4335045A
US4335045A US05/669,967 US66996776A US4335045A US 4335045 A US4335045 A US 4335045A US 66996776 A US66996776 A US 66996776A US 4335045 A US4335045 A US 4335045A
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US
United States
Prior art keywords
alkenyl
pyrrolidine
acetyl
dichloropentylamine
aminomethyl
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Expired - Lifetime
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US05/669,967
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English (en)
Inventor
Eric-Alain Denzler
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SACHIM SA A SWISS NATIONALITY
Sachim SA
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Sachim SA
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Assigned to SACHIM S.A., A SWISS NATIONALITY reassignment SACHIM S.A., A SWISS NATIONALITY ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: ERIC-ALAIN DENZLER
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical

Definitions

  • the invention concerns the preparation of N-alkenyl-2-aminomethyl-pyrrolidines, in particular N-allyl-2-aminomethylpyrrolidine.
  • N-substituted 2-aminomethyl-pyrrolidines is known for the preparation of pharmaceutically-valuable benzamides which are used as medicaments in the fields of gastro-enterology and neurology. It is however known that it is not possible, in a secondary chain of the nitrogen atom in the pyrrolidine ring, to prepare non-saturated alkenyl derivatives by treating a nitromethylene group in the ⁇ -C atom of the pyrrolidine ring by nascent hydrogen, or by catalytic hydrogenation (W. German published patent applications (DOS) Nos. 1,941,536; 1,966,195 and 2,152,371) since this would also produce hydrogenation of a non-saturated double linking in the secondary N-chain.
  • DOS German published patent applications
  • a process of preparing an N-alkenyl-2-aminomethyl pyrrolidine comprises reacting tetrahydrofurfurylamine with gaseous hydrochloric acid and thionyl chloride whereby by opening the ring 2,5-dichloropentylamine hydrochloride is obtained; this is then acetylized into N-acetyl-2,5-dichloropentylamine which is condensed by an alkenylamine into an N-alkenyl-2-acetylaminomethyl-pyrrolidine ring from which the acetyl group is separated.
  • Acetylation of the 2,5-dichloropentylamine can take place in a simple and suitable manner by means of acetyl chloride in dichloroethane in the presence of triethylamine or by means of anhydrous acetic acid. After re-closing the ring, the acetyl group can be separated in an acid or an alkaline medium.
  • a stream of gaseous hydrochloric acid is delivered by the gas delivery tube.
  • the reaction is very exothermic and the temperature rapidly reaches 100°-110° C. This temperature is maintained by cooling the flask and by adjusting the supply of gaseous hydrochloric acid. After about four hours, the gaseous hydrochloric acid is no longer absorbed.
  • the reaction mixture is cooled to 55°-60° C. and one liter of chloroform is added.
  • the gas delivery tube is replaced by a dropping funnel in which 350 ml of freshly distilled thionyl chloride is introduced.
  • the thionyl chloride is allowed to drop slowly, and the reaction mixture progressively dissolves. Reflux heating is continued for two hours, and an abundant precipitate appears.
  • the reaction mixture is allowed to cool and stand overnight.
  • the precipitate formed is filtered, washed with chloroform and the product obtained dried in a drying chamber.
US05/669,967 1975-12-19 1976-03-24 Preparation of N-alkenyl-2-aminomethyl-pyrrolidines Expired - Lifetime US4335045A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH16485/75 1975-12-19
CH1648575A CH605735A5 (bg) 1975-12-19 1975-12-19

Publications (1)

Publication Number Publication Date
US4335045A true US4335045A (en) 1982-06-15

Family

ID=4417787

Family Applications (1)

Application Number Title Priority Date Filing Date
US05/669,967 Expired - Lifetime US4335045A (en) 1975-12-19 1976-03-24 Preparation of N-alkenyl-2-aminomethyl-pyrrolidines

Country Status (36)

Country Link
US (1) US4335045A (bg)
JP (1) JPS5277057A (bg)
AR (1) AR207183A1 (bg)
AU (1) AU498596B2 (bg)
BE (1) BE839087A (bg)
BG (1) BG24228A3 (bg)
CA (1) CA1065881A (bg)
CH (1) CH605735A5 (bg)
CS (1) CS212759B2 (bg)
DD (1) DD125202A5 (bg)
DE (1) DE2623257C2 (bg)
DK (1) DK137450B (bg)
EG (1) EG12355A (bg)
FI (1) FI62068C (bg)
FR (1) FR2335501A1 (bg)
GB (1) GB1470749A (bg)
GR (1) GR59793B (bg)
HK (1) HK478A (bg)
IE (1) IE43221B1 (bg)
IL (1) IL49120A (bg)
LU (1) LU74460A1 (bg)
MC (1) MC1090A1 (bg)
MW (1) MW776A1 (bg)
MX (1) MX3088E (bg)
NL (1) NL7602533A (bg)
NO (1) NO143530C (bg)
OA (1) OA05259A (bg)
PH (1) PH12945A (bg)
PL (1) PL99929B1 (bg)
PT (1) PT64875B (bg)
RO (1) RO68461A (bg)
SE (1) SE410450B (bg)
SU (1) SU629873A3 (bg)
YU (1) YU40278B (bg)
ZA (1) ZA761407B (bg)
ZM (1) ZM3576A1 (bg)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103508986A (zh) * 2012-06-20 2014-01-15 中国石油化工股份有限公司 一种制备n,n-二甲基四氢糠胺的方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5822110B2 (ja) * 1977-08-08 1983-05-06 塩野義製薬株式会社 ベンズアミド誘導体の合成法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3597447A (en) * 1968-02-16 1971-08-03 Ile De France Process for producing 1-alkyl (or alkenyl)-2-aminoalkylpyrrolidines and intermediates therefor

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH544754A (fr) * 1972-12-21 1974-01-15 Rossier Jean Paul Procédé de préparation de la N-éthyl, 2 aminométhyl pyrrolidine
FR2229693A1 (en) * 1973-05-18 1974-12-13 Step Ste Civile Monegasque N-ethyl-2-aminomethyl pyrrolidine prepn. from hydrogen bromide - and tetrahydro furfurylamine and cyclisation with monoethylamine

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3597447A (en) * 1968-02-16 1971-08-03 Ile De France Process for producing 1-alkyl (or alkenyl)-2-aminoalkylpyrrolidines and intermediates therefor

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
Kirk-Othmer, Encyclopedia of Chemical Technology, (Second Edition, 1969), vol. 19, pp. 397-398. *
Mcomie, Advances in Organic Chemistry, Methods and Results, vol. 3, (Interscience Pub., 1963), pp. 206-210. *
Wagner et al., Synthetic Organic Chemistry, (New York, 1953), p. 566. *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103508986A (zh) * 2012-06-20 2014-01-15 中国石油化工股份有限公司 一种制备n,n-二甲基四氢糠胺的方法
CN103508986B (zh) * 2012-06-20 2015-08-12 中国石油化工股份有限公司 一种制备n,n-二甲基四氢糠胺的方法

Also Published As

Publication number Publication date
SE7602217L (sv) 1977-06-20
NL7602533A (nl) 1977-06-21
DK137450C (bg) 1978-08-14
ZA761407B (en) 1977-02-23
LU74460A1 (bg) 1976-09-01
MC1090A1 (fr) 1976-11-22
IL49120A (en) 1979-03-12
IL49120A0 (en) 1976-04-30
DE2623257C2 (de) 1981-12-17
PL99929B1 (pl) 1978-08-31
OA05259A (fr) 1981-02-28
FI62068C (fi) 1982-11-10
FR2335501B1 (bg) 1979-05-18
IE43221L (en) 1977-06-19
CH605735A5 (bg) 1978-10-13
YU40278B (en) 1985-12-31
YU67276A (en) 1982-08-31
FR2335501A1 (fr) 1977-07-15
RO68461A (ro) 1981-08-30
BE839087A (fr) 1976-07-01
NO143530C (no) 1981-03-04
HK478A (en) 1978-01-13
DK89576A (bg) 1977-06-20
PH12945A (en) 1979-10-18
AU498596B2 (en) 1979-03-15
AR207183A1 (es) 1976-09-15
SU629873A3 (ru) 1978-10-25
IE43221B1 (en) 1981-01-14
DE2623257A1 (de) 1977-06-30
NO143530B (no) 1980-11-24
PT64875B (de) 1977-07-22
NO760598L (bg) 1977-06-21
FI62068B (fi) 1982-07-30
PT64875A (de) 1976-04-01
ZM3576A1 (en) 1977-09-21
CA1065881A (en) 1979-11-06
CS212759B2 (en) 1982-03-26
JPS5277057A (en) 1977-06-29
DD125202A5 (bg) 1977-04-06
SE410450B (sv) 1979-10-15
BG24228A3 (bg) 1978-01-10
MX3088E (es) 1980-03-23
MW776A1 (en) 1977-06-08
GB1470749A (en) 1977-04-21
FI760459A (bg) 1977-06-20
DK137450B (da) 1978-03-06
EG12355A (en) 1978-12-31
GR59793B (en) 1978-02-28
AU1180076A (en) 1977-09-15

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Owner name: SACHIM S.A., 2, BOULEVARD DU THEATRE- CH 1204 GENE

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:ERIC-ALAIN DENZLER;REEL/FRAME:004174/0695

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Owner name: SACHIM S.A., A SWISS NATIONALITY, SWITZERLAND

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:ERIC-ALAIN DENZLER;REEL/FRAME:004174/0695

Effective date: 19830505